Sodium Chloride → HCID 86725299, compound

HRID 1403233Notes

Reaction equation

HRID 1403233 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:26])=[C:8]([C:10]2[NH:11][C:12]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH3:25])[N:19]=3)=[CH:13][C:14]=2[C:15]([NH2:17])=[O:16])[CH:9]=1.[CH3:27][SiH:28]([CH3:30])[CH3:29].[Na+].[Cl-].C1[CH2:37][O:36][CH2:35][CH2:34]1>>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:26])=[C:8]([C:10]2[N:11]([CH2:37][O:36][CH2:35][CH2:34][Si:28]([CH3:30])([CH3:29])[CH3:27])[C:12]([C:18]3[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH3:25])[N:19]=3)=[CH:13][C:14]=2[C:15]([NH2:17])=[O:16])[CH:9]=1

Participants

6

Reactant 5

HCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 70435TrimethylsilaneHCID 66571316HCID 66571316, compound

Product 1

HCID 86725299HCID 86725299, compoundYield 45%

Procedure

NaH (60% dispersion in mineral oil, 160 mg, 4.0 mmol) was added to a suspension of 2-(5-chloro-2-methyl-phenyl)-5-(2-methylamino-pyrimidin-4-yl)-1H-pyrrole-3-carboxamide (1.0 g, 2.92 mmol) in dry THF (15 mL) at 0° C. The reaction was kept at the same temperature for 20 min then 2-(chloromethoxy)ethyl](trimethyl)silane (0.714 mL, 4.0 mmol) was added and the mixture was stirred at room temperature for 2 h. Saturated aqueous NaCl (20 mL) was added at 0° C. and the mixture was extracted with EtOAc (2×30 mL). The separated organic phase was dried over sodium sulfate and the solvent evaporated. The crude was purified by flash chromatography on silica gel (DCM/EtOH 94/6) to afford the title compound (620 mg, 45%).

Workup

  1. extractionthe mixture was extracted with EtOAc (2×30 mL)
  2. dry with materialThe separated organic phase was dried over sodium sulfate
  3. customthe solvent evaporated
  4. customThe crude was purified by flash chromatography on silica gel (DCM/EtOH 94/6)

Sources & evidence

ORD record
ord-9d8c0acd5e614029b54f36ca24737903
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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